Ep 80: Should I Sell a Stock With a Large Taxable Gain?

You may have acquired stock and seen it significantly rise in value over time. Now you're not sure what to do: let it ride or sell, pay taxes, and reinvest in a better portfolio.

 

Astute investors know concentrated stock holdings are suboptimal and expose a portfolio to diversifiable risks. But simply selling regardless of tax consequences is also short-sighted. So how do they best fit into your portfolio and financial plan?

 

Hear Kevin discuss how to think through this complex decision. He will evaluate the costs and expected benefits of making a partial or full transition and discuss how Separately Managed Accounts or SMAs can be used as a tax-smart tool to better optimize your investments in light of concentrated or low-cost basis stock positions.

 

Even if you do not have concentrated or low-cost basis stock positions, the insights you'll get on optimizing your portfolio and drivers of its results make it worth a listen.

 

Show notes: https://www.truewealthdesign.com/ep-80-should-i-sell-a-stock-with-a-large-taxable-gain/ 

 

What we discuss on this episode: 

 

3:23 - Background on this tax scenario

8:15 - Selling out of your positions and then reinvesting

14:01 - Statistical modeling to find the best return

18:06 - Formulating the expected returns

19:21 -  What to do with legacy holdings

23:53 - The benefit of true customization 

29:57 - What to expect from your financial advisor